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Simplification of the induced circular dichroism method and its application to biologically active natural products

Research Project

Project/Area Number 18590025
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKyushu University of Health and Welfare

Principal Investigator

HOSOI Shinzo  Kyushu University of Health and Welfare, School of Pharmaceutical Sciences, Associate Professor (60209236)

Co-Investigator(Kenkyū-buntansha) SAKUSHIMA Akiyo  Kyusyu University of Health Welfare, School of Pharmaceutical Sciences, Professor (40094833)
KIUCHI Fumiyuki  National Institute of Biomedical Innovation, Research Center for Medicinal Plant Resources, Director (60161402)
TAKAHASHI Ichiro  Fukui University, Faculty of Engineering, Associate Professor (90197129)
Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,980,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥480,000)
Fiscal Year 2007: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2006: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordscircular dichroism / asymmetry / absolute configuration / molecular mechanics calculation / conformational analysis / amine / alcohol / natural products / キラル
Research Abstract

1) Circular dichroism in a chiral amide possessing an achiral bhaohthyl chromophore
The bisignate CD curves were observed at around 240 nm in all binaphthyl amides examined. In a conformational analysis of the derivatives, a close correlation was observed between the signs of exciton chirality and the screw senses of the two 2-naphthoyl groups (positive/clockwise; negative/counterclockwise). A semi-empirical molecular orbital calculation (AM1) suggested an intramolecular hydrogen bonding. The CD spectra of the antipodal amides changed into split curves centered at 225 nm after N-methylation. Furthermore, the calculated screw senses between the electric transition moments of the binaphthyl system in N-methyl amides were in good accordance with those expected from their exciton chiralities, indicating a possible application for determination of absolute configuration.
2) Induced circular dichroism and conformational analysis of 2.2'-binaphthyl esters derived from primary alcohols possessing a stereogenic center in the β-position
Induced bisignate CD curves were observed near 240 nm in all 2, 2'-binaphthyl esters derived from primary alcohols with a chiral center in the p-position of the hydroxyl group. Conformational analyses of the esters by molecular mechanics were performed. In some cases, the calculated screw sense between the two longitudinal transition moments of 2-naphthoate groups for the most stable conformer with clockwise or counterclockwise orientation was found to be different from that expected from their exciton chiralities. Therefore, CD calculations and conformational analyses of the two esters having strong or moderate interaction between the functional group of the substrate and the ester group of the 2-naphthoate were carried out by the time-dependent density functional theory (TD-DFT). The results suggested that the TD-DFT is strongly effective for determination of the absolute configuration of binaphthyl esters.

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (14 results)

All 2008 2007 2006

All Journal Article (3 results) (of which Peer Reviewed: 1 results) Presentation (11 results)

  • [Journal Article] Circular Dichroism in a Chiral Amide Possessing an Achiral Binaphthyl Chromophore2006

    • Author(s)
      S.Hosoi, J.Serata, A.Sakushima, F.Kiuchi, I.Takahashi, T.Ohta
    • Journal Title

      Letters in Organic Chemistry 3

      Pages: 58-61

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Circular Dichroism in a Chiral Amide Possessing an Achiral Binaphthyl Chromophore2006

    • Author(s)
      Shinzo Hosoi, Jun Serata, Akiyo Sakushima, Fumiyuki Kauchi, Ichiro Takahashi, Tomihisa Ohta
    • Journal Title

      Letters in Organic Chemistry 3

      Pages: 58-61

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Circular Dichroism in a Chiral Amide Possessing an Achiral Binaphthyl Chromophore2006

    • Author(s)
      S.Hoshoi, J.Serata, A.Sakushima, F.Kuichi, I.Takahashi, T.Ohta
    • Journal Title

      Letters in Organic Chemistry 3・1

      Pages: 58-61

    • Related Report
      2006 Annual Research Report
  • [Presentation] β位に不斉中心を有する一級アルコールのビナフチル誘導体の誘起CDと立体配座解析2008

    • Author(s)
      細井 信造, 佐久嶋 明世, 田中 丈幸, 木内 文之
    • Organizer
      日本薬学会第128年会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Induced circular dichroism and conformational analysis of the primary alcohol possessing a chiral stereogenic center in theβ-position2008

    • Author(s)
      Shinzo Hosoi, Akiyo Sakushima, Takeyuki Tanaka, Fumiyuki Kiuchi
    • Organizer
      The 127th Annual Meeting of the Pharmaceutical Society of Japan
    • Place of Presentation
      Yokohama, Japan
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 誘起CD励起子法のβ位に不斉中心を有する一級アルコールへの適用2007

    • Author(s)
      細井 信造, 佐久嶋 明世
    • Organizer
      第24回日本薬学会九州支部大会
    • Place of Presentation
      第一薬科大学
    • Year and Date
      2007-12-08
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Application of the induced exciton chirality method to the primary alcohol possessing a chiral stereogenic center in the β-position2007

    • Author(s)
      Shinzo Hosoi, Akiyo Sakushima
    • Organizer
      The 24th Kyushu Branch Meeting of the Pharmaceutical Society of Japan
    • Place of Presentation
      Fukuoka, Japan
    • Year and Date
      2007-12-08
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 誘起CD励起子法のβ位に不斉中心を有する一級アルコール類への適用2007

    • Author(s)
      細井 信造, 佐久嶋 明世
    • Organizer
      第24回日本薬学会九州支部大会
    • Place of Presentation
      第一薬科大学
    • Year and Date
      2007-12-08
    • Related Report
      2007 Annual Research Report
  • [Presentation] Application of the induced exciton chirality method to the primary alcohol possessing a chiral stereogenic center in theβ-position2007

    • Author(s)
      Shinzo Hosoi, Akiyo Sakushima
    • Organizer
      The 11th International Conference on Circular Dichroism
    • Place of Presentation
      Groningen, The Netherlands
    • Year and Date
      2007-09-03
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Application of the induced exciton chirality method to the primary alcohol possessing a chiral stereogenic center in the β-position2007

    • Author(s)
      Shinzo Hosoi, Akiyo Sakushima
    • Organizer
      The 11th International Conference on Circular Dichroism
    • Place of Presentation
      University of Groningen,The Netherlands
    • Year and Date
      2007-06-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] 2,2'-ビナフチルエステルにおけるアルキル置換基の誘起CDに及ぼす影響について2007

    • Author(s)
      細井 信造, 佐久嶋 明世, 太田 富久, 木内 文之
    • Organizer
      日本薬学会第127年会
    • Place of Presentation
      富山大学
    • Year and Date
      2007-03-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Influence of the alkyl substituents in 2, 2'-binaphthyl esters on the induced circular dichroism2007

    • Author(s)
      Shinzo Hosoi, Akiyo Sakushima, Tomihisa Ohta, Fumiyuki Kiuchi
    • Organizer
      The 127th Annual Meeting of the Pharmaceutical Society of Japan
    • Place of Presentation
      Toyama, Japan
    • Year and Date
      2007-03-30
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Novel method for assignment of absolute configuration based on an induced axial chirality and its application to natural products2006

    • Author(s)
      Shinzo Hosoi
    • Organizer
      The 8th Internationa Symposium on Pharmaceutical Sciences
    • Place of Presentation
      Ankara, Turkey
    • Year and Date
      2006-06-16
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Novel method for assignment of absolute configuration based on an induced axial chirality and its application to natural products2006

    • Author(s)
      Shinzo Hosoi
    • Organizer
      The 8th International Symposium on Pharmaceutical Sciences
    • Place of Presentation
      Ankara University Turkey
    • Year and Date
      2006-06-15
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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